RU2320662C1 - ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ - Google Patents
ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ Download PDFInfo
- Publication number
- RU2320662C1 RU2320662C1 RU2006130507/04A RU2006130507A RU2320662C1 RU 2320662 C1 RU2320662 C1 RU 2320662C1 RU 2006130507/04 A RU2006130507/04 A RU 2006130507/04A RU 2006130507 A RU2006130507 A RU 2006130507A RU 2320662 C1 RU2320662 C1 RU 2320662C1
- Authority
- RU
- Russia
- Prior art keywords
- general formula
- compounds
- aryl
- fluorophenyl
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 6
- 150000002475 indoles Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- -1 thiocarbonylamino group Chemical group 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 8
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 4
- 230000003287 optical effect Effects 0.000 claims abstract 4
- AIKRNPPDTQIQIZ-UHFFFAOYSA-N pyrrolo[3,4-b]indole Chemical class C1=CC=C2C3=CN=CC3=NC2=C1 AIKRNPPDTQIQIZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000011282 treatment Methods 0.000 claims abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 230000004770 neurodegeneration Effects 0.000 claims abstract 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 3
- 230000001387 anti-histamine Effects 0.000 claims 3
- 239000000739 antihistaminic agent Substances 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000000324 neuroprotective effect Effects 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 230000004936 stimulating effect Effects 0.000 claims 3
- MICHWNKGSYKDCM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrrolo[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNC2 MICHWNKGSYKDCM-UHFFFAOYSA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- QWQWXDRTKPXTSX-UHFFFAOYSA-N 2-benzyl-4-phenyl-1,3-dihydropyrrolo[3,4-b]indole Chemical compound C=1C=CC=CC=1CN(C1)CC2=C1C1=CC=CC=C1N2C1=CC=CC=C1 QWQWXDRTKPXTSX-UHFFFAOYSA-N 0.000 claims 1
- OFQYGAMGFXOSCI-UHFFFAOYSA-N 2-benzyl-7-methyl-3,4-dihydro-1h-pyrrolo[3,4-b]indole Chemical compound C1C=2C3=CC(C)=CC=C3NC=2CN1CC1=CC=CC=C1 OFQYGAMGFXOSCI-UHFFFAOYSA-N 0.000 claims 1
- ACFUEUYFWYCXGH-UHFFFAOYSA-N 4-(benzenesulfonyl)-2-[(4-methoxyphenyl)methyl]-1,3-dihydropyrrolo[3,4-b]indole Chemical compound C1=CC(OC)=CC=C1CN1CC(C=2C(=CC=CC=2)N2S(=O)(=O)C=3C=CC=CC=3)=C2C1 ACFUEUYFWYCXGH-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000000742 histaminergic effect Effects 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 230000008506 pathogenesis Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000004031 phenylhydrazines Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Toxicology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2006130507/04A RU2320662C1 (ru) | 2006-08-24 | 2006-08-24 | ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| PCT/RU2007/000435 WO2008026965A1 (fr) | 2006-08-24 | 2007-08-08 | Pyrrolo[4,3-b]indoles substitués, bibliothèques focalisées ou combinatoires, composition pharmaceutique, procédé de fabrication et d'utilisation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2006130507/04A RU2320662C1 (ru) | 2006-08-24 | 2006-08-24 | ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2320662C1 true RU2320662C1 (ru) | 2008-03-27 |
Family
ID=39136157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006130507/04A RU2320662C1 (ru) | 2006-08-24 | 2006-08-24 | ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
Country Status (2)
| Country | Link |
|---|---|
| RU (1) | RU2320662C1 (fr) |
| WO (1) | WO2008026965A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2651074T3 (es) | 2012-10-02 | 2018-01-24 | Bayer Cropscience Ag | Compuestos heterocíclicos como plaguicidas |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2104279C1 (ru) * | 1992-03-12 | 1998-02-10 | Смитклайн Бичам Плс | Конденсированное индольное производное или его фармацевтически приемлемая соль, фармацевтическая композиция, проявляющая активность антагониста 5-нт*004-рецептора |
| US6066742A (en) * | 1996-09-18 | 2000-05-23 | Kyorin Pharmaceutical Co., Ltd. | Intermediates for the preparation of duocarmycin SA and derivatives thereof, and process for the production of the intermediates |
| US6080859A (en) * | 1997-01-24 | 2000-06-27 | Kyorin Pharmaceutical Co., Ltd. | Pyrroloindole derivatives and intermediates in producing the same |
| TW491846B (en) * | 1997-01-24 | 2002-06-21 | Kyorin Seiyaku Kk | Pyrroloindole derivative and its production intermediate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968231A (en) * | 1974-04-01 | 1976-07-06 | Bayer Aktiengesellschaft | 4-Aryl-1,2,3,4-tetrahydropyrrolo(3,4-b)indoles for treating schizophrenic manifestations |
| AR207799A1 (es) * | 1974-04-01 | 1976-10-29 | Pfizer | Procedimiento para preparar azaciclo(3,4-a)-n-fenilindoles-2-substituidos |
| US4006164A (en) * | 1974-04-01 | 1977-02-01 | Pfizer Inc. | 4-Aryl-1,2,3,4-tetrahydropyrrolo[3,4-b]indoles |
| SU614108A1 (ru) * | 1976-08-01 | 1978-07-05 | Всесоюзный Научно-Исследовательский И Проектный Институт Полимерных Продуктов | Способ получени производных 2,2а,7,7а,8-тетрагидропирроло(2,8-с)-индола |
-
2006
- 2006-08-24 RU RU2006130507/04A patent/RU2320662C1/ru not_active IP Right Cessation
-
2007
- 2007-08-08 WO PCT/RU2007/000435 patent/WO2008026965A1/fr not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2104279C1 (ru) * | 1992-03-12 | 1998-02-10 | Смитклайн Бичам Плс | Конденсированное индольное производное или его фармацевтически приемлемая соль, фармацевтическая композиция, проявляющая активность антагониста 5-нт*004-рецептора |
| US6066742A (en) * | 1996-09-18 | 2000-05-23 | Kyorin Pharmaceutical Co., Ltd. | Intermediates for the preparation of duocarmycin SA and derivatives thereof, and process for the production of the intermediates |
| US6080859A (en) * | 1997-01-24 | 2000-06-27 | Kyorin Pharmaceutical Co., Ltd. | Pyrroloindole derivatives and intermediates in producing the same |
| TW491846B (en) * | 1997-01-24 | 2002-06-21 | Kyorin Seiyaku Kk | Pyrroloindole derivative and its production intermediate |
Non-Patent Citations (1)
| Title |
|---|
| ШАРКОВА Н.М. и др. Производные индола. XXVII. Тетрагидропирроло[3,4-b]индолы. Химия гетероциклических соединений, 1969, (1), 81-7. * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008026965A1 (fr) | 2008-03-06 |
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